Surely the most obvious idea is to have it pop up normally when you connect your device - with a [scrobble] button and a list of songs played, that way you can check them and you also get to know that something is being done.

My problem is that the s9 is still a bit shaky as i'm messing and deleting a lot so i'm yet to see how easy it gets.

Also surely there can be more people working on this - last.fm is open source and surely not all users use iPods - Spread the word!